Building a Macrocyclic Toolbox from C-Linked Carbohydrates Identifies Antiangiogenesis Agents from Zebrafish Assay
2013 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2013, no 23, 5036-5040 p.Article in journal (Refereed) Published
We report the synthesis of four different types of macrocyclic-derived glycohybrids from carbohydrates that have an amino acid moiety in the large-ring skeleton. These macrocyclic glycohybrids were obtained from -C-1H- and -C-1H-linked carbohydrates. In one series, we utilized ring-closing metathesis as the stitching technology to obtain two different macrocycles, i.e., trans equatorial-axial C-1H and C-5H and cis axial-axial C-1H and C-5H. The click approach was the key reaction in our second series to obtain two other macrocyclic compounds, i.e., trans equatorial-axial C-1H and C-5H and cis axial-axial C-1H and C-5H. The evaluation of this toolbox resulted in the identification of two unique compounds as antiangiogenesis agents in an embryonic zebrafish assay. Interestingly, in both cases, the macrocyclic compounds that have a cis relationship (i.e., axial-axial orientation) between C-1H and C-5H showed activity and their other diastereomers (i.e., equatorial-axial C-1H and C-5 H) with a trans relationship did not show any effect.
Place, publisher, year, edition, pages
2013. Vol. 2013, no 23, 5036-5040 p.
IdentifiersURN: urn:nbn:se:sh:diva-19664DOI: 10.1002/ejoc.201300548ISI: 000322761000008ScopusID: 2-s2.0-84885953757OAI: oai:DiVA.org:sh-19664DiVA: diva2:646038